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ID: ALA2390847

Journal: Eur J Med Chem

Title: Synthesis and biological evaluation of novel phosphatidylinositol 3-kinase inhibitors: Solubilized 4-substituted benzimidazole analogs of 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474).

Authors: Rewcastle GW, Gamage SA, Flanagan JU, Kendall JD, Denny WA, Baguley BC, Buchanan CM, Chao M, Kestell P, Kolekar S, Lee WJ, Lill CL, Malik A, Singh R, Jamieson SM, Shepherd PR.

Abstract: A range of 4-substituted derivatives of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di-(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) were prepared in a search for more soluble analogs. 4-Aminoalkoxy substituents provided the most potent derivatives, with the 4-O(CH2)3NMe2 analog (compound 14) being identified as displaying the best overall activity in combination with good aqueous solubility (25 mg/mL for the hydrochloride salt). This compound was tested in a U87MG xenograft model, but displayed less potency than ZSTK474 as a result of an unfavorable pharmacokinetic profile.

CiteXplore: 23644197

DOI: 10.1016/j.ejmech.2013.03.038